How to Date When Over 50: A Complete Guide (2020)- Aging Greatly

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Whether you are divorced, widowed, or have never been married, if you are over 50 and want to start dating, you probably want some advice about where to start.

Successful dating when you are over 50 can only happen when you are ready. You need to decide what you value and want in a partner. Learn how to let a person know you are interested and be realistic about how long it will take. Regardless of what route you choose, the key quality you need is confidence.

Dating at any age is complicated, and it does not get any easier with age. Being over 50 adds more complications. In our guide, we will navigate through some of those complications so that you come to enjoy the experience.

Why Is Dating So Hard in Your 50s?

For starters, when did you last date? If it has been more than ten years, you haven’t connected to the dating scene anymore. You have fewer single friends, the pool of available singles is smaller, and you might not be confident that you will find someone who will find you attractive.

Also, people over 50 are more set in their ways. We also carry more baggage, even if we are not divorced or widowed. And we do not have as much patience anymore—we know what we want, or think we do, and don’t have the flexibility to change ourselves as we did in our twenties.

On the other hand, you also have more experience overcoming challenges by now. Once you have a dating plan, you can use those past challenges to overcome the new ones.

Are You Really Ready to Date?

This might sound like a silly question, but before you start dating, you need to be ready. Once you decide to get back into the dating scene, you will be faced with various challenges, and you want to be ready.

Failure. You will not get everything right. Maybe your first date will bomb, or you wear the wrong outfit, or show up late?
Rejection. You are going to be putting yourself out there. What if you create a profile on a dating app, and no one responds? Or you meet someone you like, and he never returns your call?
Uncertainty. Get used to second-guessing yourself. Did I go about finding a date the right way? Should I have waited longer before calling back? Did I pick the right outfit?

If you feel ready to face the challenges, good for you, you have found the confidence needed to get started. If not, then you first need to work on being ready to face those challenges.

Finding Your Confidence

Whether you are entering the dating scene because you are divorced, widowed, or tired of being single, you will not get the dates you want until you appear confident. That’s right—looking good is important. But who are we fooling—we don’t have the looks we did when we were 25.

So, where does a +50 woman or man find her or his beauty? It comes from the belief that you are beautiful and a worthy catch. In a word, confidence.

But where does that confidence come from?

First, it comes from you being in touch with yourself. If you have lived by yourself for many years, you already have your own identity. However, if you are divorced or widowed, then you need to heal your wounds first.

You Need to Rediscover Your Authentic Self

Think about what you used to do that you stopped to accommodate your former husband or wife. Did you want to take art classes and never got around to it? Have you changed your taste in music? Was your partner always hesitant to try something new? This is your time to do those things you always wanted to but never got around to.

Look online for activities that appeal to you. Sites like Meet-Up provide opportunities to meet people who have common interests. Art centers often offer classes, local colleges have continuing-ed courses, and city or county recreation departments offer opportunities to volunteer.

As you begin to venture out and find activities you enjoy, you will begin to find your inner confidence. Reclaiming yourself will give you the inner glow you need to entice men.

Knowing When You Are Ready to Date

You know you are ready to date when you have taken on new activities that you found online or were recommended by your friends. Doing that will give you the confidence you will need as you begin dating.

But it is also essential to think about your ex. How do you feel when you do? If you are still filled with bitterness, then you have not healed. And when that happens, you will be dating, and what will you talk about when the topic of your ex comes up—and it will?

You’ll dish on your ex, and it won’t be pretty. If you have healed the wounds, you will be able to move on. But if you are still bitter, it will show. Expressing your bitterness with close friends can be an excellent way to talk through your feelings.

The goal of a date is not to work through your feelings. Most people will find the bitterness a turn-off. After all, how would you feel if all they talk about is their awful ex’s?

How to Get Started

Don’t get started by going on dates. The first step is not to sign up for an online dating service or start hanging out where you think you will meet singles.

Instead, start by thinking about what you want to get out of dating. Is it companionship, friendship, or romance? Long term or short term? Women, especially, should spend time on these questions. Remember, just because society still tries to mold us to be passive and receptive, does not mean women have to date and let the man lead. Decide what you want.

Here are several ways to do so:

Identify what you value. There are many ways to do this. Journaling is an excellent way to think through what you want. Personality tests like the Myers-Briggs or this collection by Open Psychometrics have dozens of tests to help you identify your personality type.
Decide what you do not want. Instead of thinking about what you want, think about what you don’t want in your partner. Doing this is an excellent way to come with your deal-breaker list. It should not be long—maybe four or five items—but if you are dating and things on your deal-breaker list show up, it’s time to move on.
Make a vision board. A vision board lets you create a space that reflects your values and goals. Not sure what a vision board is, then check out this Huff Post article. Have some fun with it, and host a vision board party.
Talk to others. If you wanted to change careers, you would talk to friends who work in that field. Why not do the same thing with dating? Talk to a friend or acquaintance in a healthy relationship and how they got there. Another person to talk to would be a therapist who can help you identify your values and what you want from a relationship. Psychology Today is an excellent resource with nationwide therapist listings.

How to Find A Partner

Once you decide you are ready, it is time to find a partner. But where?

One place you will not find a partner is your house. Instead, you are going to go to where the single people are. The good news is that you should already be doing the things you need—taking classes, volunteering, book clubs, or whatever else you have chosen to do.

You might have to make some adjustments if there are no single people at the activities you are going to. The yoga class you enjoy has no singles—check out Tai-Chi or another martial art.

Prime Locations for Partner-Hunting

Sure, you can find singles in almost any place. Some spots are better than others. Take an office supply store. Sure, you will find people there, but most of them will be too focused on getting supplies and leaving that getting their attention will be difficult.

Here are some other spots you might want to consider:

Grocery stores. Everybody needs to eat, right? The rescue trick—more about that in a minute—usually works better here, unless his/her cart is full of gourmet food, in which case he/she might wind up cooking for you!
Coffee shops and restaurants. Single people who aren’t cooking are eating out.
Home improvement stores. That’s a great place to fish for single men. What man doesn’t like to show off his knowledge of tools and building materials? If there’s a small project you want to be done, like hanging some shelves, asking for help on picking materials that will help the shelf stay up is a two-for-one. Not only does he show off what he knows, but he might also even want to show off his carpentry skills. Just make sure he doesn’t have a Honey-Do List.
Hair salon. Everyone needs to get their hair also cut, right? Hair salons are excellent places to strike up a conversation. Don’t forget manicures and pedicures. Especially pedicures—many would rather pay someone else to take care of their toes.
Wine shops. Going to a bar alone can be overwhelming. Wine tasting or classes don’t have the same pressure, and the single people there are not there to get laid. Cooking classes are another great option.
Sporting events. Another spot where there are men and testosterone. If you follow the team or sport, then impress the guy by talking shop—why they should not have traded so and so, or how they always blow the lead in the 8th inning.
Spots with live music. If there is a place in town that has live jazz or blues, you will likely find lots of single people.

Letting Someone Know You Are Interested

You find yourself attracted to someone in a class or at your favorite coffee shop. What now?

What you need is a signal to let him or her know that you are interested. The good news is that you always carry the signal with you—a smile.

First, you need to make eye contact. Then you smile. And here’s the hard part—smile for five seconds. That sounds like an eternity, but it’s not. If you smile and immediately look away, that person will think you aren’t interested. If you stare too long, they will think you are desperate.

Next, you should get in the habit of asking questions. Women love to talk and answer questions. Men, on the other hand, seem hard-wired to want to help women. So if you are at the coffee shop and get the guy’s attention, do not ask him if he lives around here. Instead, ask him whether he’s tried the muffins before. Or if he knows what kind of coffee they use (unless it’s obvious).

If asking questions is not something that you are comfortable with, then use the rescue technique. Drop something–keys, a package, or something else that won’t break. Let them come to your rescue.

If you’re interested in a man, use his natural tendency to want to help to your advantage no matter whether you’re in a grocery store, home improvement store, or any time you meet a single man you’re interested in.

Online Dating

For some of us, the advice to ask your friends does not work, especially not if they are all married. You might not be active in church or be involved in social events. So, where are all the eligible singles? Online, that’s where.

That is why many singles over 50 are turning to online dating. Matchmaking sites have become a nearly three billion-dollar industry. Around 30% of adults have used an online dating app, and nearly 60% of those surveyed have had positive experiences.

Most users also report that they found it easy to find attractive people who shared common interests and seemed like someone they would like to meet.

This does not mean that there aren’t some problems with online dating. Profiles can be inaccurate, background checks could be more reliable, and personal information can be hacked. However, we will discuss how to protect yourself against those dangers.

Just as important is knowing that, in this case, perception and reality do not match up. In surveys by the Pew Research Organization, nearly 50% of people who have never used online dating thought it was safe. Out of those who have used it, almost 75% found it safe to meet someone.

Why You Should Give It a Go

The best reason to give online dating a try is that you will find the single people. Maybe you will get lucky finding Mr. or Ms. Right at the supermarket or in an art class, but most of us don’t have unlimited time to wander around looking for eligible. Mr. or Ms. Right also has the same number of hours in a day, and he or she does not want to waste them sitting around waiting for someone to flirt with them.

If you are still not sure, here are some reasons to try online dating:

Free time. If you work, then your free time is limited. Checking out profiles is much more convenient and efficient.
Comfort. You might be one of those who do not like going out to eat alone or participating in single’s parties.
Money. Going out costs. Those wine tastings, sporting events, and restaurants can get expensive quickly. Most dating sites will offer a free trial period or a menu of items you can pay for. For the price of a dinner, you can get access to a service with thousands of singles to pick from.
Limited choices. If you live in a small town or the ‘burbs, the pickings might be slim. You might be frustrated by the lack of available people in your town. Chances are that people in nearby small towns are just as frustrated as you.
Awkward in large settings. Some of us don’t like being in a crowd. We prefer a one-on-one conversation where we can hear and be heard. Online dating is a way to avoid the crowd.
Goal-Oriented. If you know what you want, then looking for singles who will share your goals and values will be more efficient online.

If some of these appeal to you, then it’s time to pick a site, set up your profile, and find a date.

How to Pick a Site

With hundreds of sites to pick from, how do you know which one is right for you? Let’s look at the types of dating services available. For a more extensive article about this, check our other article: 7 Best Dating Sites for Women Over 50.

Free vs. Paid Membership

On free sites, anyone can sign up without paying a monthly membership fee. Sites like Plenty of Fish and OKCupid let you sign up, create a profile, and start searching for single people for free. All members can send and receive emails. These sites offer additional services for a fee.

Paid membership sites, like Match, EHarmony, and Chemistry, require that you pay a monthly fee. Do not be fooled by the “free” feature because you will be limited in what you can do. You will set up your profile, start finding interesting people, and then need to pay to be able to send or receive emails.

There are pros and cons to both. Free sites are a great way to get started, but you have less control over who can contact you. Paid membership sites are more secure, but their numbers are misleading because they count anyone who has signed up as a potential member.

General Population vs. Niche Focus

Some sites cater to the general population, while others focus on specific niches. Some cater to a particular religion, ethnicity, or sexual orientation. Several services focus on the 50+ niche, including SilverSingles, and OurTime.

The nice thing about these niche focus services is they eliminate people you are not interested in. If you are not planning on dating anyone under 50, for example, then a niche site will exclude all those guys and girls in their 20s and 30s. The flip side is that niche sites have a smaller selection.

Rather than recommend a specific site, here are a few suggestions to keep in mind:

The vibe. Check out different sites and get a feel for the vibe. For example, if you go to the PlentyofFish site, you might like the simple design and laid back feel, or you might wonder why all the people look like they are in their thirties.
Don’t overextend yourself. Although you might be tempted to sign up for three or four, don’t. If you are on several sites simultaneously, it’s going to be challenging to keep track of everything. Also, sites tend to flag new users. When your profile gets activated is when you will get the most attention.
Give it some time. Don’t expect overnight results. Stay with a site for a month to get a feel for how the whole online dating scene works. Then you can stick with that one or add a second niche site.

Tips on Setting Up a Profile

The work you have so far on finding your confidence and deciding what you want will pay off as you start on your profile. To create an excellent profile, you need to think about your online dating brand, have an attractive picture, and write a profile that gets and keeps your potential suitor’s attention.

A Picture Used to Be Worth a Thousand Words

We all know that pictures are important. Guys and girls will be evaluating you based on your looks, but so will you. That intense pressure has probably got you worried. If you do not feel confident about how your pictures will look, relax. You are not alone. Women and men on dating sites all feel your pain.

Here are a few things to keep in mind:

Present yourself as a person. Go ahead and have a headshot or two—make sure to look at the camera and smile that flirty smile you have been practicing. Then add pictures that show you doing what you love doing. Keep in mind that people will think that what you do in your profile pictures is what you like. If you are showing cleavage and drinking, many will assume you want to hook-up.
Keep your pictures honest and timely. Don’t post a picture of yourself in your forties. You don’t want someone to be dishonest with you, so do the same. If you are worried about how you will look, maybe it’s time to get a make-over. Ask your hairdresser for advice on what hairstyle would look good on you.
Don’t go overboard. Shoot for five to ten pictures, even if the site lets you post more. The goal of your photos is to create interest. Have a headshot, add a full-body photograph, an activity-based photo, and a picture of you away from home. Be doing something in your full-body picture.
Learn from Hollywood. The best headshot for someone over 50 is looking up at the camera. You will need to get a friend to climb a ladder. No need for cleavage—look into the picture and smile.

Your Profile Is Only As Good as Your Writing

If someone’s picture is a turn-off, then move on to the next one. But if the person looks so-so or better, then quickly move on to what they have written.

When writing your essay, keep your target audience in mind. You aren’t trying to appeal to everyone. Think about your ideal partner and write a description of what he or she is like. Then keep those notes handy as you write.

Be clear about what you want to do and write vivid descriptions about things you like doing. You want the person to see herself doing these things with you.

And keep your baggage out. If you hate your job or your ex, it doesn’t belong. Avoid complaining about the process of finding dates online.

For more advice on writing good profiles, check out the competition. Some dating sites let you browse for free. Browse the women’s or men’s profiles to get the other perspective.

Safety Tip: Along with leaving out the obvious things in your profile—name, address, phone number—also keep your workplace, church, places you regularly hang out, and your living arrangements to yourself.

If You Don’t Want to Go Online, Try One of These Options

The whole online thing might seem overwhelming, or maybe you are too busy to invest the time. Many people rely on matchmakers or dating coaches to help them find men to date.

Matchmaking Services or Independent Matchmakers

Matchmaking has a long history that is shared in many traditions. There is evidence that even the Aztecs used matchmakers. Today you can find individual matchmakers or larger services that connect you with personal matchmakers.

These companies have a more rigorous, vetting process. Since the cost can be $5,000 or more, potential matches tend to be wealthier. Using a matchmaking service will screen dates and save you a lot of time if you have the money.

Dating Coaches

A dating coach spends more time coaching you through the process. This person can advise on how to find singles, attract them, and decide whether you want to use online dating apps. Using a coach is no guarantee you will be successful finding a partner, but having someone guide you through the process can help you succeed.

Coaches often charge an hourly rate. There is an accreditation process for dating coaches, so make sure whoever you select has accreditation.

Some dating coaches blur the line by also offering matchmaking services for additional fees.

Bottom Line

Dating is never easy, but it should be fun. Make sure you are ready to date, find your inner confidence, and be realistic—you will meet many singles, and some are going to be duds. Don’t worry—many wonderful people are looking for an attractive, funny, smart person like you. They are also going through the same frustrations as you. It’s just a matter of time until the two of you meet.

How to Date When Over 50: A Complete Guide